Ceric ammonium nitrate → HCID 18932707, compound

HRID 1452401Notes

Reaction equation

HRID 1452401 reaction equation
[CH2:1]([CH:3]1[CH2:12][C:11]2[C:6](=[C:7]([O:15]C)[CH:8]=[CH:9][C:10]=2[O:13]C)[CH2:5][O:4]1)[CH3:2].O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>C(#N)C>[O:13]=[C:10]1[CH:9]=[CH:8][C:7](=[O:15])[C:6]2[CH2:5][O:4][CH:3]([CH2:1][CH3:2])[CH2:12][C:11]1=2

Participants

4

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 18932616HCID 18932616, compound

Product 1

HCID 18932707HCID 18932707, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-ethyl-5,8-dimethoxy-isochroman (300 mg; 1.35 mmol) in acetonitrile (10 ml) at room temperature was added dropwise a solution of CAN (prepared by dissolving ceric ammonium nitrate (2.22 g; 4.0 mmol) in water (5 ml)). The resulting mixture was quenched with saturated bicarbonate solution and extracted with dichloromethane. The combined organic layers were washed with brine and dried over Na2SO4 affording the crude title compound (251 mg; 97%) which was used as such for subsequent steps.

Workup

  1. customThe resulting mixture was quenched with saturated bicarbonate solution
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4 affording the crude title compound (251 mg; 97%) which

Sources & evidence

ORD record
ord-e55da98af97746d4b4503d9ca9788fa9
Source dataset
uspto-grants-1997_02
Patent number
US05606037

Reaction notes

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